JP4964396B2 - オレフィン重合用触媒成分 - Google Patents
オレフィン重合用触媒成分 Download PDFInfo
- Publication number
- JP4964396B2 JP4964396B2 JP2002534381A JP2002534381A JP4964396B2 JP 4964396 B2 JP4964396 B2 JP 4964396B2 JP 2002534381 A JP2002534381 A JP 2002534381A JP 2002534381 A JP2002534381 A JP 2002534381A JP 4964396 B2 JP4964396 B2 JP 4964396B2
- Authority
- JP
- Japan
- Prior art keywords
- electron donating
- groups
- succinic acid
- catalyst component
- extractable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000003054 catalyst Substances 0.000 title claims description 27
- 238000006116 polymerization reaction Methods 0.000 title claims description 23
- 150000001336 alkenes Chemical class 0.000 title claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 239000011949 solid catalyst Substances 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229920001155 polypropylene Polymers 0.000 claims description 8
- 150000003900 succinic acid esters Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000003609 titanium compounds Chemical class 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 150000002902 organometallic compounds Chemical class 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 25
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 21
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 19
- -1 polypropylene Polymers 0.000 description 16
- 239000011777 magnesium Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- 239000008096 xylene Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000010936 titanium Substances 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
- 229910052749 magnesium Inorganic materials 0.000 description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 7
- 229910001629 magnesium chloride Inorganic materials 0.000 description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- 150000004756 silanes Chemical class 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 4
- 229920006378 biaxially oriented polypropylene Polymers 0.000 description 4
- 239000011127 biaxially oriented polypropylene Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000011147 magnesium chloride Nutrition 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229940078552 o-xylene Drugs 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910003074 TiCl4 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- WNVMVIYFKFGESM-UHFFFAOYSA-N bis(2-methylpropyl) 2,3-di(propan-2-yl)butanedioate Chemical compound CC(C)COC(=O)C(C(C)C)C(C(C)C)C(=O)OCC(C)C WNVMVIYFKFGESM-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- IPKKHRVROFYTEK-UHFFFAOYSA-N dipentyl phthalate Chemical compound CCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCC IPKKHRVROFYTEK-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 238000004438 BET method Methods 0.000 description 2
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 2
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- WGFNXLQURMLAGC-UHFFFAOYSA-N diethyl 2,3-di(propan-2-yl)butanedioate Chemical compound CCOC(=O)C(C(C)C)C(C(C)C)C(=O)OCC WGFNXLQURMLAGC-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- MQHNKCZKNAJROC-UHFFFAOYSA-N dipropyl phthalate Chemical compound CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- PJSFQEVODHCOOF-UHFFFAOYSA-N (2-ethylpiperidin-1-yl)-dimethoxy-(3,3,3-trifluoropropyl)silane Chemical compound CCC1CCCCN1[Si](CCC(F)(F)F)(OC)OC PJSFQEVODHCOOF-UHFFFAOYSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- POXXQVSKWJPZNO-UHFFFAOYSA-N 1-o-ethyl 2-o-(2-methylpropyl) benzene-1,2-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC(C)C POXXQVSKWJPZNO-UHFFFAOYSA-N 0.000 description 1
- DUAYDERMVQWIJD-UHFFFAOYSA-N 2-n,2-n,6-trimethyl-1,3,5-triazine-2,4-diamine Chemical compound CN(C)C1=NC(C)=NC(N)=N1 DUAYDERMVQWIJD-UHFFFAOYSA-N 0.000 description 1
- JEABIFHLYSDNRJ-UHFFFAOYSA-N 2-o-butyl 1-o-ethyl benzene-1,2-dicarboxylate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC JEABIFHLYSDNRJ-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- KYZHGEFMXZOSJN-UHFFFAOYSA-N benzoic acid isobutyl ester Natural products CC(C)COC(=O)C1=CC=CC=C1 KYZHGEFMXZOSJN-UHFFFAOYSA-N 0.000 description 1
- FPGRDBPTRVSBLF-UHFFFAOYSA-N bis(2-methylpropyl) 2,2-dimethylbutanedioate Chemical compound CC(C)COC(=O)CC(C)(C)C(=O)OCC(C)C FPGRDBPTRVSBLF-UHFFFAOYSA-N 0.000 description 1
- AXBODPMRFMDTMR-UHFFFAOYSA-N bis(2-methylpropyl) 2-(cyclohexylmethyl)-2-(2-methylpropyl)butanedioate Chemical compound CC(C)COC(=O)CC(CC(C)C)(C(=O)OCC(C)C)CC1CCCCC1 AXBODPMRFMDTMR-UHFFFAOYSA-N 0.000 description 1
- LMBDNTZGGDKOQY-UHFFFAOYSA-N bis(2-methylpropyl) 2-cyclopentyl-2-propylbutanedioate Chemical compound CC(C)COC(=O)CC(CCC)(C(=O)OCC(C)C)C1CCCC1 LMBDNTZGGDKOQY-UHFFFAOYSA-N 0.000 description 1
- RQRAFBDBIOAJDS-UHFFFAOYSA-N bis(2-methylpropyl) 2-ethyl-2-methylbutanedioate Chemical compound CC(C)COC(=O)C(C)(CC)CC(=O)OCC(C)C RQRAFBDBIOAJDS-UHFFFAOYSA-N 0.000 description 1
- KBRYDKFNMPLCEB-UHFFFAOYSA-N bis(2-methylpropyl) 2-propan-2-ylbutanedioate Chemical compound CC(C)COC(=O)CC(C(C)C)C(=O)OCC(C)C KBRYDKFNMPLCEB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OOSZILWKTQCRSZ-UHFFFAOYSA-N butyl-dimethoxy-methylsilane Chemical compound CCCC[Si](C)(OC)OC OOSZILWKTQCRSZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- GWUJPMKBSYJFCK-UHFFFAOYSA-N decyl-dimethoxy-methylsilane Chemical compound CCCCCCCCCC[Si](C)(OC)OC GWUJPMKBSYJFCK-UHFFFAOYSA-N 0.000 description 1
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 1
- REHGOUOFAJQGSN-UHFFFAOYSA-N diethyl 2,2-bis(2-methylpropyl)butanedioate Chemical compound CCOC(=O)CC(CC(C)C)(CC(C)C)C(=O)OCC REHGOUOFAJQGSN-UHFFFAOYSA-N 0.000 description 1
- DODIKAULZAKDIN-UHFFFAOYSA-N diethyl 2,2-dimethylbutanedioate Chemical compound CCOC(=O)CC(C)(C)C(=O)OCC DODIKAULZAKDIN-UHFFFAOYSA-N 0.000 description 1
- YCYHZGIPKZHEEL-UHFFFAOYSA-N diethyl 2,3-bis(2,2-dimethylpropyl)butanedioate Chemical class CCOC(=O)C(CC(C)(C)C)C(CC(C)(C)C)C(=O)OCC YCYHZGIPKZHEEL-UHFFFAOYSA-N 0.000 description 1
- ZEKAIFREAFGGIC-UHFFFAOYSA-N diethyl 2,3-bis(2-ethylbutyl)butanedioate Chemical compound CCOC(=O)C(CC(CC)CC)C(CC(CC)CC)C(=O)OCC ZEKAIFREAFGGIC-UHFFFAOYSA-N 0.000 description 1
- AVLHXEDOBYYTGV-UHFFFAOYSA-N diethyl 2,3-bis(2-methylpropyl)butanedioate Chemical compound CCOC(=O)C(CC(C)C)C(CC(C)C)C(=O)OCC AVLHXEDOBYYTGV-UHFFFAOYSA-N 0.000 description 1
- FITPXUCDWCINLG-UHFFFAOYSA-N diethyl 2,3-bis(cyclohexylmethyl)butanedioate Chemical compound C1CCCCC1CC(C(=O)OCC)C(C(=O)OCC)CC1CCCCC1 FITPXUCDWCINLG-UHFFFAOYSA-N 0.000 description 1
- OTUNNRWESSPIBH-UHFFFAOYSA-N diethyl 2,3-bis(trimethylsilyl)butanedioate Chemical compound CCOC(=O)C([Si](C)(C)C)C([Si](C)(C)C)C(=O)OCC OTUNNRWESSPIBH-UHFFFAOYSA-N 0.000 description 1
- UIZHEHICSUOPQL-UHFFFAOYSA-N diethyl 2,3-dibenzylbutanedioate Chemical compound C=1C=CC=CC=1CC(C(=O)OCC)C(C(=O)OCC)CC1=CC=CC=C1 UIZHEHICSUOPQL-UHFFFAOYSA-N 0.000 description 1
- CXKANZAMPQTLBJ-UHFFFAOYSA-N diethyl 2,3-dicyclohexylbutanedioate Chemical compound C1CCCCC1C(C(=O)OCC)C(C(=O)OCC)C1CCCCC1 CXKANZAMPQTLBJ-UHFFFAOYSA-N 0.000 description 1
- ISOWAXIPBFLPIC-UHFFFAOYSA-N diethyl 2,3-dicyclopentylbutanedioate Chemical compound C1CCCC1C(C(=O)OCC)C(C(=O)OCC)C1CCCC1 ISOWAXIPBFLPIC-UHFFFAOYSA-N 0.000 description 1
- QILIJPUOBXQLLC-UHFFFAOYSA-N diethyl 2-(2-methylpropyl)butanedioate Chemical compound CCOC(=O)CC(CC(C)C)C(=O)OCC QILIJPUOBXQLLC-UHFFFAOYSA-N 0.000 description 1
- OKFRLPHKPXFFBE-UHFFFAOYSA-N diethyl 2-(4-chlorophenyl)butanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)C1=CC=C(Cl)C=C1 OKFRLPHKPXFFBE-UHFFFAOYSA-N 0.000 description 1
- GBEDNFHCEKAPAV-UHFFFAOYSA-N diethyl 2-(4-methoxyphenyl)butanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)C1=CC=C(OC)C=C1 GBEDNFHCEKAPAV-UHFFFAOYSA-N 0.000 description 1
- URZDPTYHEBVBEZ-UHFFFAOYSA-N diethyl 2-(cyclohexylmethyl)-2-(2-methylpropyl)butanedioate Chemical compound CCOC(=O)CC(CC(C)C)(C(=O)OCC)CC1CCCCC1 URZDPTYHEBVBEZ-UHFFFAOYSA-N 0.000 description 1
- GRVYPVYGTIWYIC-UHFFFAOYSA-N diethyl 2-(cyclohexylmethyl)butanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)CC1CCCCC1 GRVYPVYGTIWYIC-UHFFFAOYSA-N 0.000 description 1
- TXRNMKWGVBBYLW-UHFFFAOYSA-N diethyl 2-benzyl-2-propan-2-ylbutanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)(C(C)C)CC1=CC=CC=C1 TXRNMKWGVBBYLW-UHFFFAOYSA-N 0.000 description 1
- JZJPBADSXBZWAZ-UHFFFAOYSA-N diethyl 2-benzylbutanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)CC1=CC=CC=C1 JZJPBADSXBZWAZ-UHFFFAOYSA-N 0.000 description 1
- UKZUISCHPZZJME-UHFFFAOYSA-N diethyl 2-butan-2-ylbutanedioate Chemical compound CCOC(=O)CC(C(C)CC)C(=O)OCC UKZUISCHPZZJME-UHFFFAOYSA-N 0.000 description 1
- GKCJIKJXEOGKJU-UHFFFAOYSA-N diethyl 2-butyl-2-phenylbutanedioate Chemical compound CCOC(=O)CC(CCCC)(C(=O)OCC)C1=CC=CC=C1 GKCJIKJXEOGKJU-UHFFFAOYSA-N 0.000 description 1
- CSCAPDXCOWYRFM-UHFFFAOYSA-N diethyl 2-cyclohexyl-2-ethylbutanedioate Chemical compound CCOC(=O)CC(CC)(C(=O)OCC)C1CCCCC1 CSCAPDXCOWYRFM-UHFFFAOYSA-N 0.000 description 1
- RQPNECGZAMRIRP-UHFFFAOYSA-N diethyl 2-cyclohexylbutanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)C1CCCCC1 RQPNECGZAMRIRP-UHFFFAOYSA-N 0.000 description 1
- NLLYHAKHAPQUBQ-UHFFFAOYSA-N diethyl 2-cyclopentyl-2-propylbutanedioate Chemical compound CCOC(=O)CC(CCC)(C(=O)OCC)C1CCCC1 NLLYHAKHAPQUBQ-UHFFFAOYSA-N 0.000 description 1
- XMVGCOWCTAZJNT-UHFFFAOYSA-N diethyl 2-cyclopropylbutanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)C1CC1 XMVGCOWCTAZJNT-UHFFFAOYSA-N 0.000 description 1
- DJHQJVJMROPIHP-UHFFFAOYSA-N diethyl 2-ethyl-2-methylbutanedioate Chemical compound CCOC(=O)CC(C)(CC)C(=O)OCC DJHQJVJMROPIHP-UHFFFAOYSA-N 0.000 description 1
- CRFNZTOCCSXWQM-UHFFFAOYSA-N diethyl 2-methoxybutanedioate Chemical compound CCOC(=O)CC(OC)C(=O)OCC CRFNZTOCCSXWQM-UHFFFAOYSA-N 0.000 description 1
- NIVYXGURCVRNKN-UHFFFAOYSA-N diethyl 2-methyl-2-(1,1,1-trifluoropropan-2-yl)butanedioate Chemical compound CCOC(=O)CC(C)(C(C)C(F)(F)F)C(=O)OCC NIVYXGURCVRNKN-UHFFFAOYSA-N 0.000 description 1
- CNVQQORAGNTULF-UHFFFAOYSA-N diethyl 2-methyl-2-propan-2-ylbutanedioate Chemical compound CCOC(=O)CC(C)(C(C)C)C(=O)OCC CNVQQORAGNTULF-UHFFFAOYSA-N 0.000 description 1
- JVQDNCKPHSZFSO-UHFFFAOYSA-N diethyl 2-phenylbutanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)C1=CC=CC=C1 JVQDNCKPHSZFSO-UHFFFAOYSA-N 0.000 description 1
- SSQLHHBLAVHVOU-UHFFFAOYSA-N diethyl 2-propan-2-ylbutanedioate Chemical compound CCOC(=O)CC(C(C)C)C(=O)OCC SSQLHHBLAVHVOU-UHFFFAOYSA-N 0.000 description 1
- ZRCLPPMOEHAMRP-UHFFFAOYSA-N diethyl 2-tert-butylbutanedioate Chemical compound CCOC(=O)CC(C(C)(C)C)C(=O)OCC ZRCLPPMOEHAMRP-UHFFFAOYSA-N 0.000 description 1
- AQFKFFFGIFNPMT-UHFFFAOYSA-N diethyl 2-trimethylsilylbutanedioate Chemical compound CCOC(=O)CC([Si](C)(C)C)C(=O)OCC AQFKFFFGIFNPMT-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- DIJRHOZMLZRNLM-UHFFFAOYSA-N dimethoxy-methyl-(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](C)(OC)CCC(F)(F)F DIJRHOZMLZRNLM-UHFFFAOYSA-N 0.000 description 1
- UNDUWLPONQBXSZ-UHFFFAOYSA-N dimethoxy-methyl-pentylsilane Chemical compound CCCCC[Si](C)(OC)OC UNDUWLPONQBXSZ-UHFFFAOYSA-N 0.000 description 1
- XKRPWHZLROBLDI-UHFFFAOYSA-N dimethoxy-methyl-propylsilane Chemical compound CCC[Si](C)(OC)OC XKRPWHZLROBLDI-UHFFFAOYSA-N 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- APQKDJQPCPXLQL-UHFFFAOYSA-N hexyl-dimethoxy-methylsilane Chemical compound CCCCCC[Si](C)(OC)OC APQKDJQPCPXLQL-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000009862 microstructural analysis Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920001384 propylene homopolymer Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000012721 stereospecific polymerization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/646—Catalysts comprising at least two different metals, in metallic form or as compounds thereof, in addition to the component covered by group C08F4/64
- C08F4/6465—Catalysts comprising at least two different metals, in metallic form or as compounds thereof, in addition to the component covered by group C08F4/64 containing silicium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/04—Broad molecular weight distribution, i.e. Mw/Mn > 6
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00203535.0 | 2000-10-13 | ||
EP00203535 | 2000-10-13 | ||
PCT/EP2001/011048 WO2002030998A1 (en) | 2000-10-13 | 2001-09-24 | Catalyst components for the polymerization of olefins |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2004511590A JP2004511590A (ja) | 2004-04-15 |
JP2004511590A5 JP2004511590A5 (de) | 2008-10-23 |
JP4964396B2 true JP4964396B2 (ja) | 2012-06-27 |
Family
ID=8172130
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002534381A Expired - Fee Related JP4964396B2 (ja) | 2000-10-13 | 2001-09-24 | オレフィン重合用触媒成分 |
Country Status (21)
Country | Link |
---|---|
US (2) | US6825309B2 (de) |
EP (1) | EP1272533B1 (de) |
JP (1) | JP4964396B2 (de) |
KR (1) | KR100899958B1 (de) |
CN (2) | CN1221573C (de) |
AR (1) | AR030989A1 (de) |
AT (1) | ATE407153T1 (de) |
AU (1) | AU781278B2 (de) |
BR (1) | BR0107335B1 (de) |
CA (1) | CA2396232C (de) |
DE (1) | DE60135643D1 (de) |
ES (1) | ES2312484T3 (de) |
HU (1) | HUP0204041A3 (de) |
MX (1) | MXPA02005825A (de) |
MY (1) | MY128622A (de) |
PL (1) | PL355609A1 (de) |
RU (1) | RU2279442C2 (de) |
SA (1) | SA01220540B1 (de) |
TW (1) | TWI289144B (de) |
WO (1) | WO2002030998A1 (de) |
ZA (1) | ZA200204396B (de) |
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BR0306195B1 (pt) * | 2002-08-01 | 2012-12-25 | processo para a preparaÇço de polÍmeros, polÍmeros obtidos pelo mesmo, filmes ou folhas e artigos laminados multicamadas. | |
TWI253451B (en) * | 2002-08-29 | 2006-04-21 | Toho Catalyst Co Ltd | Solid catalyst component, catalyst for polymerization of olefins, and polymerizing method of olefins |
US7541402B2 (en) * | 2002-10-15 | 2009-06-02 | Exxonmobil Chemical Patents Inc. | Blend functionalized polyolefin adhesive |
US7550528B2 (en) * | 2002-10-15 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | Functionalized olefin polymers |
KR101113341B1 (ko) * | 2002-10-15 | 2012-09-27 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 올레핀 중합용 다중 촉매 시스템 및 이로부터 제조된중합체 |
US7700707B2 (en) * | 2002-10-15 | 2010-04-20 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
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WO2005113672A1 (en) | 2004-05-21 | 2005-12-01 | Basell Poliolefine Italia S.R.L. | Impact resistant polyolefin compositions |
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CN1328293C (zh) * | 2004-09-02 | 2007-07-25 | 中国石油化工股份有限公司 | 用于烯烃聚合反应的催化剂组分和催化剂 |
CN1318457C (zh) * | 2004-09-02 | 2007-05-30 | 中国石油化工股份有限公司 | 用于烯烃聚合反应的催化剂组分和催化剂 |
EP1797138B2 (de) | 2004-10-04 | 2017-08-16 | Basell Poliolefine Italia S.r.l. | Elastomerpolyolefinzusammensetzungen |
JP4688135B2 (ja) * | 2005-01-18 | 2011-05-25 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分および触媒 |
US7888438B2 (en) | 2005-01-19 | 2011-02-15 | Mitsui Chemicals, Inc. | Catalyst for olefin polymerization and process for olefin polymerization |
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JP4632299B2 (ja) * | 2005-01-26 | 2011-02-16 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分、その製造方法および触媒 |
JP2008528779A (ja) | 2005-02-03 | 2008-07-31 | バーゼル・ポリオレフィン・イタリア・ソチエタ・ア・レスポンサビリタ・リミタータ | 射出成形用プロピレンポリマー組成物 |
US8513366B2 (en) * | 2005-03-17 | 2013-08-20 | University Of Maryland, College Park | Methods for modulated degenerative transfer living polymerization and isotactic-atactic stereoblock and stereogradient poly(olefins) thereby |
EP1871832B1 (de) * | 2005-04-21 | 2012-06-13 | Basell Poliolefine Italia S.r.l. | Biaxial orientierte propylenpolymerfolien |
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AU1589702A (en) | 2002-04-22 |
ES2312484T3 (es) | 2009-03-01 |
US20030060581A1 (en) | 2003-03-27 |
BR0107335B1 (pt) | 2011-09-06 |
AU781278B2 (en) | 2005-05-12 |
CA2396232C (en) | 2011-09-20 |
CA2396232A1 (en) | 2002-04-18 |
TWI289144B (en) | 2007-11-01 |
KR100899958B1 (ko) | 2009-05-28 |
EP1272533B1 (de) | 2008-09-03 |
WO2002030998A1 (en) | 2002-04-18 |
PL355609A1 (en) | 2004-05-04 |
SA01220540B1 (ar) | 2008-03-23 |
HUP0204041A3 (en) | 2004-08-30 |
JP2004511590A (ja) | 2004-04-15 |
MY128622A (en) | 2007-02-28 |
US20050131172A1 (en) | 2005-06-16 |
CN1221573C (zh) | 2005-10-05 |
RU2002118701A (ru) | 2004-01-10 |
CN1721455A (zh) | 2006-01-18 |
KR20020063217A (ko) | 2002-08-01 |
ZA200204396B (en) | 2003-11-26 |
ATE407153T1 (de) | 2008-09-15 |
MXPA02005825A (es) | 2003-10-14 |
HUP0204041A2 (hu) | 2003-03-28 |
BR0107335A (pt) | 2002-08-27 |
RU2279442C2 (ru) | 2006-07-10 |
US7169871B2 (en) | 2007-01-30 |
CN1398270A (zh) | 2003-02-19 |
AR030989A1 (es) | 2003-09-03 |
US6825309B2 (en) | 2004-11-30 |
EP1272533A1 (de) | 2003-01-08 |
DE60135643D1 (de) | 2008-10-16 |
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